Warden-x-Reader: Love by the Watchtower Light
by Otakutater0724
Summary: You're an inmate at Ultraprison, run by the notorious Mistress. She has a rival who runs another jail...a Superjail to be exact and the ruler of this establishment is none other than The Warden...you were drafted to go in undercover and learn all his tricks and recipes, but what he was really was cooking up was love.
1. Being Drafted

You stood in line beside the other female inmates with their voluptuous forms. They wore very skimpy clothes for being criminals, you on the other hand chose the same blue colors in a simple pair of sweatpants and a t-shirt. Most of them were arrested for whoring, drug possession, murder, or other terrible crimes...but you were here under false charges.

You were a well behaved criminal studies college student whose professor was doing some really bad things with the other female students as "course practice" that would've had him arrested by normal standards, but you were the only one who was quiet and simple enough to ignore his advances and see through his facade and he made it seem like you were coming onto him when suspicions were finally filed against him, which lead to your arrest.

Your body wasn't as developed as your surrounding inmates, you were very flat chested, plain faced, and wore rectangular, pink lensed glasses to help your vision focus on letters and crazy, different things your vision used to do as you grew up.

"Now! Here's the plan, we need a way to invade Superjail and gain control of it from the idiotic grasp of that childish, immature, and pathetic man...The Warden!" A woman's voice boomed from in front of you a few girls down. Your eyes wandered past your glasses to see…The Mistress.

She was wearing a yellow sleeveless dress shirt with a high collar, a green tie hung from her neck, pink shorts being held up by pink suspenders over her shoulders, pink heeled boots with yellow socks peeking just over the tops, white gloves covered her hands, a pink hat with a flower nestled at an angle on the top, and round pink lensed glasses...similar to yours.

You shook in nervousness at her intimidating nature as she slapped a horse-whip against her hand like a general in the army, she meant business when it came to her competition the infamous Warden of Superjail. Apparently they were once a "thing" and she hated him ever since, but you weren't under Ultraprison's rule-of-terror back then.

"We need someone to go in under their radar and get all the information they can on all of The Warden's newest methods of inmate "crowd control"... now I know most of you won't do it after the party incident but Bruce here has personally expressed distaste for this mission and requested that he not do it." Her heels clicked as she walked up and down the line holding the horse-whip behind her back.

You were growing uncomfortable as she walked closer and closer to you, then as if remembering you were even a member of her flock she paused in front of you.

"You!" She pointed the horse-whip right between your eyes.

"Me?" You pointed to yourself while shaking.

"Yes, you...you're the least...um," She tapped her chin thoughtfully trying to find the right word.

"Physically developed, ma'am." Cherise, a red beehive hairdo, short woman spoke up from behind The Mistress.

"Thank you, Cherise." Mistress replied shooing her back a few inches.

"You're welcome, ma'am." Cherise cowered just as much as you did.

"I-I can't be put in a place surrounded by men...a man is why I'm here in the first place!" You whisper-shouted.

Mistress raised an eyebrow at your outburst and hatched a plan right in that short amount of time, "If you do this, I'll count it as time served against your sentence so it can be shortened." A grin formed on her face.

Your eyes flicked left-to-right under your glasses as you processed what she had said. Could she do that? She is the patron of Ultraprison, whatever she says goes even if it's on records and you could be done sooner than you thought with yours.


	2. Male-Makeover

You were led to a very plain room that had a sink, a desk chair, and a table with some supplies on it, you were shoved into the chair by Bruce, it rocked back on it's wheeled-legs with force.

"C-cut her hair into a short pixie style, but just short enough to pass in Superjail, and give her an orange jumpsuit, then have NOVA give her a few tattoos of her choice to help blend her in...o-okay?" Cherise said nervously going down the list on a clipboard that the Mistress had given her.

"Got it." Bruce said with his arms crossed and a bored look on his face as Cherise left you to his mercy.

You trembled as Bruce kick-rolled the chair over to a sink that was settled in the corner of the room, he then pulled a lever under the seat that tilted it back at an angle against the sink basin. You huffed as the force knocked a bit of breath out of you, but this was it...no turning back now, your sentence depended on it.

The cold water poured over your head as Bruce roughly shampooed, conditioned, and rinsed your hair out. He brought over a towel and dried it, but that was just the end of the first step because then he walked over to the table and plugged in a pair of hair clippers. You were rolled over closer to the table to do the next part, and that's when you heard the awful buzzing right next to your ears. Your eyes shut as you felt piles and piles of hair fall to the cold floor around you, then you heard snipping from scissors that cleaned up the edges of whatever horrible haircut you were being forcefully given.

"Here." Bruce said gruffly as you felt something hard shoved against your flat-chest.

Your eyes opened as you saw a mirror laying there, waiting to be picked up.

"What do you think?" He asked plainly.

You held the mirror up slowly as not to be too terrified when you'd see the hack job that was done to your once (h/c) decent-length hair, "I-it's…" You looked and your eyes widened in shock, "...Actually not that bad." You beamed with a sense of relief.

Your hair was short around the ears, fluffy around the top, and V-shaped at the top of your neck. You noticed your glasses had gotten some hair-flecks stuck to them and quickly took them off to wipe the pink lenses off with the towel that was used to dry your hair and keep the flecks off your clothes. Bruce was almost smiling at the response to his otherwise "manly" work but seeing as how no one else seemed to care that he was a female at one point, you were actually impressed at the feminine skill of haircutting he seemed to possess.

"Good, cause we're not one-hundred percent done yet." He rolled the chair over to another corner of the room with a hard push that kinda made you a bit dizzy, "Nova! We're ready for you!" He yelled out into the room.

With that the pink, flat bodied, robot with a human face floated in and asked in the robotic tone it usually had,

"What tattoos would you like and where?" She questioned readying a tattoo needle.

"Um...I'm not a big tattoo person, I-I actually have a fear of needles." You stuttered looking at the machine with terror.

"The Mistress has instructed me to give you tattoos that would be befitting of that of a Superjail male inmate of your choice from this sheet." Nova added with a strict tone handing you a piece of paper with some decently rebel-ish looking designs on it.

Your eyes darted left and right trying to think of something, whether it be something to get out of this part of the deal or a way to make it less painful for you to tolerate even if you **had** to choose a tattoo, "C-could you numb the spots before you do them?" You had a faint hope in your eyes that she would.

Nova looked at you with a deadpan expression then sighed in compliance, "Yes, I can do that if you so wish."

You sighed in relief at this and listed a few of the designs you thought would look ok after this whole fiasco was over and then picked the semi-visible locations they would be placed on your body. 'These robots have no respect for humans or their pains and fears.' You thought to yourself as Nova numbed and inked away paying you no mind while doing so, then left after she was finished.

A while later you were told to dress in an orange jumpsuit like those at Superjail, how Mistress had gotten one was beyond anyone's knowledge but yet she had one in her possession. Bruce turned around so you could change, 'How very gentlemanly of him.' you thought sarcastically.

It was actually a decent fit, didn't drag on the floor or smother your hands in the sleeves. You decided you would alter it later when you actually assessed personally what Superjail was like, but it was going to be a while longer before you even got that far.


	3. Dropped Off

Having been primped, pricked, and suited up for Superjail you were looked over by the Mistress with extensive critique.

She tapped her gloved index finger against her lips thoughtfully, "She seems to be ready at least to a basic standpoint," She looked you over inch-by-inch, head-to-toe, and was trying to figure out what was so off about you, then it hit her, "Ah-ha! Those glasses, they'll never do in a pigsty such as Superjail." She reached for your glasses resting against your nose.

Your eyes widened in horror as you flinched back and your arms rose to protect your face, "NO!" Your eyes sealed shut as your arms rose, "I...I can't, my vision is very fragile without them, words and things drift around and I can't focus on things...please," Your eyes opened slowly with tears starting to form, "Don't take them from me." You panted.

The Mistress looked at Cherise who was shyly standing behind her, "Ma'am, I h-have to agree with her on that one. The reason you, me and yes, even the Warden have color-lens glasses is that we have vision problems that would most likely revert optical progress if our glasses were to be removed for a long time such as that of how long you intend (y/n) to reside in Superjail."

The Mistress glared at Cherise for mentioning that manchild in her presence, but then she sighed and crossed her arms, "I guess you've made a point, Cherise." Mistress rolled her eyes in defeat.

"Other than that, ma'am. I believe she is ready to be integrated into the enemy territory." Cherise nervously smiled with a hint of humor in her words.

You looked between the two of them lowering your arms from their shielded position, this was it. You were finally going to be shipped out and attempt to blend into the most dangerous territory you have ever known. The plan was gone over very scrutinizingly, Nova was going to fly you over with a message for Warden stating that you (a male inmate) were accidentally apprehended and taken to Ultraprison instead and was being returned to Superjail, they give you a tape recorder hidden in your jumpsuit to record the information that you were being sent to retrieve, and you report to the Mistress if anything goes straight to hell.

Nova grabbed your ankle faster than you expected and lifted you upside down off the ground and started for Superjail.

-Time Skip-

Nova crashed through the roof and right into Warden's office, with the vibrations from the debris Warden flinched into a semi-fetal position in his office chair,

"WHAT THE HELL!?" He yelled into the dust that settled on the floor.

Nova held your unconscious body limply by the ankle with your glasses quite askew and said in her cold robotic tone, "We have had an apparent mix up, The Mistress sends me to return the missing inmate of yours that was accidentally sent to us."

Warden slowly straightened out from his little ball and sat up right in his chair with a thoughtful look on his face, "I don't remember anything about any new inmates. We haven't gotten any in weeks…" He paused and almost seemed to be contemplating why this would've happened, but then his expression snapped to a cheerful one, "Oh well then, I guess I'll have Jared deal with getting their information squared away...JARED! IN MY OFFICE!" He yelled into a desk microphone that had just magically appeared, "AND BRING JAILBOT WITH YOU!" He added.

Nova laid you on the floor and Jailbot crashed in through the big window behind the Warden, Jared ran in through the door sweating up a storm worried about why he was ordered into Warden's office so urgently. His eyes scanned the room and his jaw dropped at the state of the mess that scattered the room, Jailbot beeped happily when he saw Nova hovering in the room but he seemed to ignore your limp body on the floor.

"Jared, Nova here has told me about a mix up in an arrest they were sent that was supposed to be here…" He glared at Jared through his yellow glasses, "Why would there be any reason for a mistake of this caliber?"

Jared scrambled in a new found panic, "Well, I-I wish I knew sir, we haven't gotten any new inmates for weeks."

"I know that, Jared!" Warden scolded coldly with drawn out sarcasm, "I want to know **HOW** it happened!"

Jared ran out of the room and within a flash came running back in with a stack of papers, he flopped them on the floor and started to rummage through them. Warden tapped his foot impatiently on the floor as he leaned back in his chair and crossed his arms, he then looked at Nova and with break neck speed stated,

"I'm so sorry for the incompetence of my lackey, he's always like this when shit usually hits the fan at his own expense." Warden folded his hands in a polite way apologizing on behalf of the fact he usually tries to act somewhat demurely when it comes to the scornful-respect him and the Mistress share with each other.

Nova shifted her body downward in a nod, "It's okay, I do have other things to attend to at the Mistress's request so if you don't mind I will leave this inmate here and be on my way."

Warden looked at her with wide eyes behind his glasses, "Y-you...what!? You're leaving him here?" He leaned back so hard in his chair that the wheels kicked up off the floor and his gloved hand facepalmed his forehead with a groan of annoyance, "Fine! Just go and have as nice a day as a robot can have doing errands for that woman." He waved her off with his hand as she flew off through the hole in the ceiling she had made.

Warden looked at Jailbot, "Clean hers and your mess up please…" He pointed to the ceiling and window respectively, "And Jared!" He yelled at the man who was still searching through the files, "Just forget that for now and get them into a cell will you? They're starting to look like a bad throw rug." As he walked over and tapped you with his shoe and you started to groan and your eyes twitched under your pink lenses.


	4. Waking up in Superjail

Your head ached, as your eyes slowly fluttered open and winced at the bright light above you. You don't remember what exactly happened after NOVA picked you up and dangled you like a fish on a hook, but the blood that rushed down into your head must've made you pass out cold. You got up a bit too quickly and all the blood rushed back down your spine with a wave of light headed nausea and pain from your temples.

"Ahhhh!" You shuddered as you held your head stable when the nausea hit.

You sat up with your legs crossed on the bed to assess your location...you were in a concrete jail cell, this was a little different than Ultraprison's cells. It had blue walls with a few shelves, another bed on the other side of the room with no one on it, and semi-narrow bars that at your size, could easily slip through if you wanted to. You turned and placed your feet solidly on the floor to stabilize yourself, then padded over to the bars and wrapped your hands around them and quietly stuck your head through the bars and gazed up and down the halls when almost out of nowhere a flash of yellow was right in front of your eyes.

"WELL, HELLO….IT SEEMS YOU'RE AWAKE!" The Warden beamed with excitement.

"AHHHHHHH!" You screamed and jumped back onto the cold concrete landing on your butt.

He laughed boisterously and the round top of his cane turned into a cartoon-ish glove and picked you up by the back of your collar and stood you back on your feet and dusted you off with a pat and then went back to his normal cane, "I'm sorry...I just get so ecstatic when I meet a new inmate...mistakes or not."

You stared at him dumbfoundedly…"Mistakes? How many times does this usually happen?"

He taps his chin thoughtfully with his cane, "Honestly if I could keep count, 'but that's Jared's job'...it would probably be a decently low occurrence." He added the part about Jared with a flourish of his gloved hand.

You shyly held your hands behind your back and rocked on your heels, "Sooooo...do you have a name, or do they just call you "The Warden"?"

"Even if I had a real name...I wouldn't tell it to an inmate, that's dangerous you know?" He winked jokingly while mocking your stance but both his hands wrapped around his cane horizontally.

"Ah…" You paused, "So you don't want to know my name?" You asked innocently.

"Why on Earth would that matter? After all you are just a number here, at least until you make a name for yourself among the other inmates that is." He laughed with tears falling from behind his glasses.

You looked at your breast where a number was patched in where there wasn't one before, you were confused…"What do you mean a name among the inmates?" You questioned him.

"A lot of the inmates have earned their places among their peers, some have names like…

Jacknife

Gary & Bird

Jean-Baptiste Le Ghei

Paul Guaye

Fatty

Nicky

Turban

Ash Firin

Lord Stingray

Skinny

Sweet Cheeks

Tony

Rod

Bobo

Charlie Streyt

Bagpipe

Guns

Slim

Lowbrow

Pappy

So if you can earn your place, you should be just fine here in Superjail." He counted each name on fingers that magically appeared besides the ten he had.

You rubbed your eyes in disbelief, you had never seen a human do things like this...that is if the Warden was even human at all. He stood there puffed up like a proud bird who just preened his own feathers. You weren't sure that this was such a good idea anymore just to get time taken off your sentence, you just stood there dumbfounded by this purple, pink, and yellow suited gentleman with a complex.

"So, lunch will be served in a few minutes and your cell door will automatically unlock then you can follow the others in this cell block down to the cafeteria." He beamed with a bright gapped smile that you just now noticed since his mouth had been moving this whole time that you never saw the gap right in the middle of his face.

You stifled a giggle at this dork-ish gap and took a deep breath to compose yourself, "Thank you, sir."

His smile faded quickly, "Do NOT call me 'Sir'...I am The Warden and you will address me as everyone else does...do you understand me?" His voice went from warm to cold in 2 seconds flat.

Your eyes widened in a bit of unexpected terror, "Y-yes Warden." You stuttered in response.

"Good...Now, I will leave you to get more adjusted to your home here at Superjail...oh and a reminder for you," He paused after his tone had suddenly returned to it's sunny mood, "No one leaves Superjail...EVER." He added with an ominous and cheery combo, "Well...toodles." He sauntered off whistling a tune and swinging his cane in circles like a parade leader (A/N: his own ego parade maybe lol XD).

You stood there very confused by this man that just nealy scared the crap out of you just by being himself, 'He was very...unsettling.' you thought to yourself as you but your back against the bars (that you could easily fit through) and slid down the the floor. You placed your arms on your knees and sunk you head down between the hole like a nest and just sighed deeply, processing everything that has just occured since you awoke.

All of a sudden you hear a buzzing alarm and the cell door slides away from your back and you unexpectedly roll like a turtle onto your back and sprawl out into the hallway, an announcement sounds over the PA system.

"LUNCH TODAY WILL BE MYSTERY SOUP, CRACKERS, AND YOUR CHOICE OF POSSIBLY DRINKABLE FLUIDS."

You stared at the ceiling as you heard footsteps marching from the other cells coming towards your unattended head, quickly lifting yourself up you see a line of burly, tattooed, some of them uglier than others… inmates lined up and heading down a specific path down the cafeteria. 'This will be just like school all over again...I hope.' You think as you stand up and find the end of the line that was walking down your hall. You followed the line to the cafeteria and get in the line to get your food...food that looks barely...edible.


End file.
